Diethyl 2-benzylpropanedioate → 2-Benzylpropane-1,3-diol

HRID 2420143

반응식

HRID 2420143 반응식
[CH2:1]([CH:8]([C:14](OCC)=[O:15])[C:9](OCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([CH:8]([CH2:9][OH:10])[CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 69090Diethyl 2-benzylpropanedioateHCID 21226445Aluminium lithium hydride

생성물 1

HCID 5202412-Benzylpropane-1,3-diol

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Diethyl benzylmalonate (100g.) was added dropwise to a stirred suspension of lithium aluminium hydride (12g.) in anhydrous diethyl ether (300ml.) at 0° C. under argon. The reaction mixture was then stirred overnight at room temperature and worked up by the conventional procedure, described in J. Org. Chem. 1953, 18, 1190. Evaporation of the ether solution gave 2-benzylpropane-1,3-diol. Phosphorus tribromide (26ml.) was added dropwise to this diol (44g.), whilst stirring at 75° C. After the vigorous reaction had ceased, the temperature was raised to 100° C. and maintained at this temperature overnight. The cooled mixture was poured into ice water (500ml.) and extracted with diethyl ether (2 × 500ml.). The combined ether extracts were washed with aqueous sodium bicarbonate, then brine, dried over sodium sulphate and the ether was evaporated. Distillation of the crude product in vacuo gave 2-benzyl-1,3-dibromopropane b.p. 116°-121° C./1.0 mm. Hg.

후처리

  1. customEvaporation of the ether solution

출처 및 근거

ORD 기록
ord-00d8f7f9095846cdb2bcfdf35853a30e
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04109015

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